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#$Date: 2025-01-23 04:17:41 +0200 (Thu, 23 Jan 2025) $
#$Revision: 297434 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/98/7249824.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7249824
loop_
_publ_author_name
'Cifuentes, Carlos'
'Bravo, Nestor'
'Restrepo, Daniel'
'Macías, Mario'
'Portilla, Jaime'
_publ_section_title
;
 Isomerization of pirazolopyrimidines to pyrazolopyridines by
 ring-opening/closing reaction in aqueous NaOH
;
_journal_issue                   3
_journal_name_full               'RSC Advances'
_journal_page_first              2078
_journal_page_last               2085
_journal_paper_doi               10.1039/D4RA06345G
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C15 H13 N3 O'
_chemical_formula_sum            'C15 H13 N3 O'
_chemical_formula_weight         251.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-05-27 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                95.113(6)
_cell_angle_beta                 98.415(8)
_cell_angle_gamma                90.754(8)
_cell_formula_units_Z            2
_cell_length_a                   6.9160(8)
_cell_length_b                   8.9551(8)
_cell_length_c                   10.3411(6)
_cell_measurement_reflns_used    4298
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      75.9840
_cell_measurement_theta_min      4.3430
_cell_volume                     630.82(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7396
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.567
_diffrn_reflns_theta_min         4.340
_diffrn_source
'SuperNova (Cu) micro-focus sealed X-ray Source'
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0715P)²+0.1393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2259
_reflns_number_total             2594
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra06345g2.cif
_cod_data_source_block           Compound_3a
_cod_database_code               7249824
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.863
_shelx_estimated_absorpt_t_max   0.886
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N8 N 0.24331(19) 0.18619(14) 0.42375(13) 0.0466(3) Uani 1 1 d . . . . .
N6 N 0.2308(2) -0.04692(14) 0.28943(13) 0.0473(3) Uani 1 1 d . . . . .
C7 C 0.24033(19) 0.03606(16) 0.40551(15) 0.0411(3) Uani 1 1 d . . . . .
N5 N 0.2304(2) -0.19731(14) 0.30615(14) 0.0502(3) Uani 1 1 d . . . . .
C3 C 0.2463(2) -0.06464(15) 0.50345(15) 0.0420(3) Uani 1 1 d . . . . .
O11 O 0.2314(3) 0.14481(15) 0.88072(13) 0.0768(4) Uani 1 1 d . . . . .
C1 C 0.2563(2) 0.15034(16) 0.65624(15) 0.0435(3) Uani 1 1 d . . . . .
C2 C 0.2527(2) -0.00469(16) 0.63244(15) 0.0438(3) Uani 1 1 d . . . . .
H2 H 0.254455 -0.066154 0.700482 0.053 Uiso 1 1 calc R U . . .
C9 C 0.2518(2) 0.23835(16) 0.54897(16) 0.0460(3) Uani 1 1 d . . . . .
H9 H 0.254984 0.341959 0.567663 0.055 Uiso 1 1 calc R U . . .
C4 C 0.2398(2) -0.20941(17) 0.43317(17) 0.0470(4) Uani 1 1 d . . . . .
C10 C 0.2544(2) 0.22090(18) 0.79177(16) 0.0506(4) Uani 1 1 d . . . . .
C14 C 0.2784(2) 0.38799(18) 0.81847(15) 0.0497(4) Uani 1 1 d . . . . .
C18 C 0.4816(3) 0.6102(2) 0.8457(2) 0.0714(5) Uani 1 1 d . . . . .
H18 H 0.602180 0.656508 0.843631 0.086 Uiso 1 1 calc R U . . .
C15 C 0.1264(3) 0.4719(2) 0.8550(2) 0.0700(5) Uani 1 1 d . . . . .
H15 H 0.006493 0.425778 0.859330 0.084 Uiso 1 1 calc R U . . .
C12 C 0.2250(3) 0.0032(2) 0.15959(17) 0.0635(5) Uani 1 1 d . . . . .
H12A H 0.207805 0.109648 0.163880 0.095 Uiso 1 1 calc R U . . .
H12B H 0.118001 -0.046521 0.101408 0.095 Uiso 1 1 calc R U . . .
H12C H 0.345466 -0.020252 0.127439 0.095 Uiso 1 1 calc R U . . .
C19 C 0.4563(3) 0.4584(2) 0.81295(19) 0.0612(5) Uani 1 1 d . . . . .
H19 H 0.558827 0.402730 0.786998 0.073 Uiso 1 1 calc R U . . .
C13 C 0.2444(3) -0.35861(18) 0.4867(2) 0.0612(5) Uani 1 1 d . . . . .
H13A H 0.214832 -0.435977 0.415740 0.092 Uiso 1 1 calc R U . . .
H13B H 0.149133 -0.362792 0.545196 0.092 Uiso 1 1 calc R U . . .
H13C H 0.372121 -0.373203 0.533554 0.092 Uiso 1 1 calc R U . . .
C17 C 0.3295(4) 0.6943(2) 0.88155(19) 0.0728(6) Uani 1 1 d . . . . .
H17 H 0.346608 0.797101 0.903133 0.087 Uiso 1 1 calc R U . . .
C16 C 0.1532(4) 0.6254(2) 0.8852(2) 0.0814(6) Uani 1 1 d . . . . .
H16 H 0.049815 0.682254 0.908187 0.098 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N8 C7 113.27(13) . . ?
C7 N6 N5 110.93(13) . . ?
C7 N6 C12 128.70(14) . . ?
N5 N6 C12 120.36(14) . . ?
N8 C7 N6 126.11(14) . . ?
N8 C7 C3 126.72(14) . . ?
N6 C7 C3 107.17(13) . . ?
C4 N5 N6 107.08(13) . . ?
C2 C3 C7 117.80(13) . . ?
C2 C3 C4 137.77(14) . . ?
C7 C3 C4 104.42(14) . . ?
C2 C1 C9 118.83(14) . . ?
C2 C1 C10 119.94(14) . . ?
C9 C1 C10 121.15(14) . . ?
C3 C2 C1 117.56(13) . . ?
N8 C9 C1 125.81(14) . . ?
N5 C4 C3 110.40(14) . . ?
N5 C4 C13 121.42(15) . . ?
C3 C4 C13 128.18(16) . . ?
O11 C10 C1 120.84(15) . . ?
O11 C10 C14 119.81(15) . . ?
C1 C10 C14 119.35(14) . . ?
C15 C14 C19 119.44(16) . . ?
C15 C14 C10 120.12(16) . . ?
C19 C14 C10 120.36(15) . . ?
C19 C18 C17 120.35(19) . . ?
C14 C15 C16 119.59(19) . . ?
C18 C19 C14 120.23(18) . . ?
C16 C17 C18 119.50(18) . . ?
C17 C16 C15 120.9(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N8 C9 1.330(2) . ?
N8 C7 1.3403(19) . ?
N6 C7 1.347(2) . ?
N6 N5 1.3730(18) . ?
N6 C12 1.449(2) . ?
C7 C3 1.412(2) . ?
N5 C4 1.320(2) . ?
C3 C2 1.387(2) . ?
C3 C4 1.425(2) . ?
O11 C10 1.219(2) . ?
C1 C2 1.387(2) . ?
C1 C9 1.414(2) . ?
C1 C10 1.487(2) . ?
C4 C13 1.490(2) . ?
C10 C14 1.500(2) . ?
C14 C15 1.378(3) . ?
C14 C19 1.386(2) . ?
C18 C19 1.374(3) . ?
C18 C17 1.377(3) . ?
C15 C16 1.386(3) . ?
C17 C16 1.366(3) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N8 C7 N6 179.56(14) . . . . ?
C9 N8 C7 C3 -0.4(2) . . . . ?
N5 N6 C7 N8 -179.99(13) . . . . ?
C12 N6 C7 N8 1.1(3) . . . . ?
N5 N6 C7 C3 -0.05(16) . . . . ?
C12 N6 C7 C3 -178.92(15) . . . . ?
C7 N6 N5 C4 -0.05(17) . . . . ?
C12 N6 N5 C4 178.93(15) . . . . ?
N8 C7 C3 C2 1.1(2) . . . . ?
N6 C7 C3 C2 -178.79(12) . . . . ?
N8 C7 C3 C4 -179.95(14) . . . . ?
N6 C7 C3 C4 0.12(15) . . . . ?
C7 C3 C2 C1 -1.1(2) . . . . ?
C4 C3 C2 C1 -179.56(16) . . . . ?
C9 C1 C2 C3 0.5(2) . . . . ?
C10 C1 C2 C3 177.30(13) . . . . ?
C7 N8 C9 C1 -0.4(2) . . . . ?
C2 C1 C9 N8 0.3(2) . . . . ?
C10 C1 C9 N8 -176.46(14) . . . . ?
N6 N5 C4 C3 0.12(17) . . . . ?
N6 N5 C4 C13 -179.30(14) . . . . ?
C2 C3 C4 N5 178.42(16) . . . . ?
C7 C3 C4 N5 -0.15(16) . . . . ?
C2 C3 C4 C13 -2.2(3) . . . . ?
C7 C3 C4 C13 179.22(15) . . . . ?
C2 C1 C10 O11 -6.8(2) . . . . ?
C9 C1 C10 O11 169.91(16) . . . . ?
C2 C1 C10 C14 173.98(14) . . . . ?
C9 C1 C10 C14 -9.3(2) . . . . ?
O11 C10 C14 C15 -65.4(2) . . . . ?
C1 C10 C14 C15 113.83(19) . . . . ?
O11 C10 C14 C19 111.4(2) . . . . ?
C1 C10 C14 C19 -69.3(2) . . . . ?
C19 C14 C15 C16 0.2(3) . . . . ?
C10 C14 C15 C16 177.09(19) . . . . ?
C17 C18 C19 C14 -1.4(3) . . . . ?
C15 C14 C19 C18 1.1(3) . . . . ?
C10 C14 C19 C18 -175.79(17) . . . . ?
C19 C18 C17 C16 0.4(3) . . . . ?
C18 C17 C16 C15 0.9(4) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
